Exploiting the Reactivity of 1,2-Ketoamides: Enantioselective Syn-thesis of Functionalized Pyrrolidines and Pyrrolo-1,4-benzodiaze-pine-2,5-diones

Paola Acosta (1) , Diana Becerra (2) , Sébastien Goudedranche (2) , Jairo Quiroga (1) , Thierry Constantieux (2) , Damien Bonne (2) , Jean Rodriguez (2)

1 Facultad de Ciencias Exactas y Naturales
2 ISM2 - Institut des Sciences Moléculaires de Marseille

A new strategy for the synthesis of optically active pyrrolo[ 1,4]benzo- diazepine-2,5-diones has been developed. The approach is based on an initial Michael addition of functionalized 1,2-ketoamides on nitroalkenes, with a reduction–double cyclization sequence leading to the desired substituted benzodiazepine.

Keywords: benzodiazepine; 1 2-ketoamides; enantioselective Michael addition

Domains: Organic chemistry

Paola Acosta, Diana Becerra, Sébastien Goudedranche, Jairo Quiroga, Thierry Constantieux, et al.. Exploiting the Reactivity of 1,2-Ketoamides: Enantioselective Syn-thesis of Functionalized Pyrrolidines and Pyrrolo-1,4-benzodiaze-pine-2,5-diones. SYNLETT, 2015, 26, pp.1591-1595. ⟨10.1055/s-0034-1378711⟩. ⟨hal-01219398⟩